Unattainable
by Agent in Lilac
Summary: Chuck Bass was astonished. That girl had not only turned him down, but she had figured him out and told him off without batting an eye." Chuck fic!
1. Chapter 1

**Gossip Girl Fan Fic**

**Agent in Lilac**

**I do not own Gossip Girl or any of its Characters.**

**Chapter One**

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Chuck Bass leaned arrogantly against the bar, gazing out over the party scene in front of him. It was the night of the notorious "Falling Back" party, celebrating the first day of October. The music was blaring, and dimmed lights created a scandalous atmosphere as bodies danced wildly to the music.

"Evening, Chuck," a familiar voice said.

Chuck turned to his left, though he already knew who was talking to him. James Harrington. Spiky gelled hair, muscular build, shifty eyes. James was a player, very similar to Chuck Bass himself. Although the boys shared a competitive friendship, Chuck enjoyed having James around. Nate didn't always approve of Chuck's playboy lifestyle, a lifestyle that James embraced wholeheartedly. It was nice to have a guy around to party and pick up chicks with.

"Redhead, three o'clock," James stated, pointing out a girl with a super tight green dress. Her dress was low-cut and incredible short. James mentioned the excess cleavage the girl had obviously aimed for and mouthed, "Bull's-eye."

Chuck grinned. "Nice pick." The two boys always picked out a girl (or sometimes two) to hook up with at parties. It was a sort of game between them, although neither had been turned down before.

Chuck scanned the room, looking for possibilities. The brunette with the leopard dress? The blonde with the trashy red lipstick? Nobody especially appealed to him, but he didn't have high standards, so just an ordinary girl would work for one night.

He was about to pick the brunette, but scanned the room one last time, just in case. Suddenly, a girl caught his eye, and he paused, completely mesmerized.

The girl was slowly walking down the wide marble stairs that led to the party room. Her black dress hugged her slim frame and she moved gracefully atop towering, strappy gold stilettos. Her shiny blonde hair was completely straight and her bangs were perfectly in place. She paused for a moment on the stairs, gazing around the room.

Chuck smiled triumphantly. "I choose her," he declared.

James looked in his line of vision and gave a low whistle. "Wow," he exclaimed, somehow making the word three syllables. "She must be new; I definitely would have remembered her."

Apparently, the two boys weren't the only admirers of this new girl. Boys all around the party were craning their necks to get a look at her. Chuck noticed this with satisfaction; there was nothing he loved more than a challenge. A new girl that all the guys were after? Perfect.

James downed the last of his drink and stood up. "Got to say man, nice target for the night. Good luck." They both laughed, perfectly confident that they would score that night. James nodded to Chuck and headed over to his redhead. James liked a direct approach to the ladies, while Chuck preferred a more subtle tactic. He decided to finish his whiskey and proceed with his usual strategy: dance with another girl within the target's view, make the target jealous, take the target home. It was foolproof and had never failed in the past.

While he finished his drink, he casually watched the blonde girl. Apparently, she didn't know anyone there, so he watched her introduce herself to different groups and hang out with everyone. Chuck was impressed by her confidence; most upper-east side girls didn't stray beyond their own clique of friends.

Just as Chuck decided to go and dance, the blonde girl made her way over to the bar and sat in the seat that James had previously occupied. Chuck grinned; this made his plan easier and more convenient.

He looked down at his empty glass and watched the girl out of the corner of his eye. "Water, please," the girl ordered. The bartender looked at her and stumbled before hurrying to get her a bottled water. Chuck rolled his eyes; it took the same bartender ten minutes to get his drink.

The girl grabbed her water and turned around, glancing over the party scene. Chuck realized she wasn't going to speak to him, so he decided to make the first move.

"Crazy, isn't it?" he remarked.

The girl smiled and turned toward him. "I know- I'm impressed. My first New York party this year," she stated.

Chuck smirked; the girl was fresh meat. If she was new, then she couldn't know that Chuck Bass was bad news: her loss, his gain.

"New to the City, huh?" he asked. "Need someone to show you around?"

The girl looked at him in surprise. "Really? That'd be great," she replied, though her voice had a slight edge of suspicion in it.

They both stood up and started walking toward the middle of the dance floor, still continuing their conversation.

Chuck started dancing a little bit and leaned toward the girl. "I'm very knowledgeable about the City," he said, dropping his voice to make it seductive. "In fact, there's a room over there where we can go and 'explore' a little bit."

The girl froze; her casual face faded into one of anger and disgust. "No," she bluntly stated.

Chuck stopped; this girl was rejecting him? That had _never_ happened before. He decided she was trying to play hard to get and laughed. "Oh I see- you just need some time to get used to the Bass," he responded confidently.

The blonde's face changed into a coy expression. "You know," she sexily whispered into Chuck's ear, "If I were a tease, I would get all really close to you like this," she continued, pressing their bodies together and wrapping her leg around his. "And then I would invite you back to that side room with me to 'explore' as much as you wanted… And then I'd never show up. "

Chuck's head was spinning and his breathing became ragged. It took him a moment to understand the meaning of the girl's last statement. The girl seemed to notice, because she stepped away from him and said in an assertive voice, "But I'm not a tease like that, so let me get my point across. I know exactly what kind of guy you are. One night stands aren't my thing, so you better go find some skank to mess around with tonight. I'm not that type of girl; I have better things to do than to be some notch on your bedpost."

And with that, she promptly turned around and headed out. Several people shouted goodbye to her and she smilingly waved back to them. Chuck stared dumbfounded after her as she nimbly walked back up the marble stairs and out into a waiting limo.

Chuck Bass was astonished. That girl had not only turned him down, but she had figured him out and told him off without batting an eye. He finally re-gained his composure and headed over to the brunette girl he spotted earlier, still thinking of his first rejection ever.


	2. Chapter 2: Need a Lift?

**Gossip Girl**

**Unattainable**

**Chapter Two**

**Do I really need to say it? I don't own Gossip Girl or else Dan and Serena would be back together already!**

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Chuck Bass reclined in his limo, enjoying his usual leisurely rides around the city. It had become a sort of habit for him; every weekend morning he headed out to relax. After all, even Chuck Bass needed some alone time.

A shrill beeping rang loudly throughout the limo and Chuck picked up his sleek silver cell phone, expertly navigating the buttons until he reached his messages. It was early in the morning and he already had three messages. What could Chuck say- he was a popular guy. Chuck smirked at his little joke and scrolled to the first message.

_"Hi Chuck, it's Blair. I was going to catch you at the party last night but I couldn't find you, which is a shame because I looked fabulous in that new D&G purple dress… But anyway, don't plan anything with Nate because I'm surprising him with a special date! He doesn't know what we're doing yet, but I'm thinking of maybe heading out of the city for a couple hours and--" _Chuck pressed 'delete' on his phone. Blair's messages were always the same; she blurted out what she wanted in the beginning and then rambled on about Blair stuff until the phone cut her off. Chuck liked the girl, but her obsessions with shoes and clothes got old. Really old.

So Blair had a big date with Nathaniel? Chuck smiled to himself; little did she know, Chuck and Nate were having a "guys night out." James had told Chuck of a trendy new pub in the city and Chuck wanted to bring Nate to check it out. Chuck smirked again; Blair would be disappointed that her plans wouldn't work out.

He moved onward to the next voice message. _"Um… Chuck? It's Nate. Look, I know we had plans for tonight, but Blair has a surprise planned and she's really excited about it. I don't want to disappoint her… and we can go to that pub later this weekend… maybe tomorrow night? Sorry man and I'll see you later." _

Chuck sighed as he deleted Nate's apologetic message. He should have known. Of course Nate would give in to Blair's plans over his own; Nate was completely whipped. It was one of the few things the two best friends disagreed about: Nate thought there was nothing wrong with having a serious steady girlfriend, while Chuck couldn't understand why he would ever want to limit himself to one girl. Girls were so predictable; he needed to change them up to keep from getting too bored and unsatisfied.

_"Hey sexy, it's Audrey, from last night. I wanted to say that I miss you and we should--"_

Chuck quickly deleted this message too. This is exactly what he meant about girls being predictable. They knew each night that it was a fling, but come morning, they all wanted to turn casual sex into a "relationship." Chuck shuddered at the word; how could he ever pin himself down to only one person?

He pressed a few buttons on the phone, exiting out of his voice mails. Normally, he would have called James to brag on how they both scored the night before. It was a little routine with them now, but Chuck didn't feel like talking about last night to James. Sure, he took that brunette Audrey girl home, but she wasn't the girl he had picked out for the evening. He squinted his brows together; for some reason, the blonde girl's rejection still ticked him off. It bothered him now more than ever, because it distracted him from truly enjoying last night.

He asked the driver to turn on some music; he needed a distraction from his wounded pride. The sound of the radio quietly flooded the limo. Chuck's favorite song was playing but he wasn't paying too much attention. He just thought and stared out the window. The traffic was especially heavy today, so it was fun to study the people passing by on the sidewalk.

He saw a frantic-looking woman trying to keep up with two toddlers, an old man running on the sidewalk, a teenage girl staggering under the weight of carrying tons of heavy bags… Chuck lingered on the last person. _Nice ass_, he thought in typical Chuck fashion.

The girl stumbled but caught herself before she fell. Chuck got a quick glance at her face and his eyes widened. _The girl from last night_…

Without thinking, Chuck ordered his driver to pull the limo over. "Hey, do you need a lift?" he shouted.

The girl turned around and scowled as she recognized him. "No, not from you," she retorted, turning away to start walking. In the process, one of her several large, heavy bags fell to the ground and its contents scattered everywhere. This fall served as a catalyst; the falling bag broke the fragile balance she had previously maintained: one dropping bag led to the rest of them falling too. The girl's face flushed and she bent down to pick up all the strewn bags.

Chuck smiled to himself: half because he had never seen the confident girl flustered like this before and half because he knew he could now get the girl to accept his offer for a ride. "You sure about that 'no?'" he called out.

The girl initially flashed him an impatient look, then sighed and reluctantly opened the limo door. It took her a couple minutes to get all the scattered objects from the sidewalk but finally, she slid inside the limo.

"Usually, I don't get rides from strangers," she said sarcastically. Usually, Chuck would have gotten angry for a comment like that, but a pink blush still colored the girl's cheeks and he knew that she was trying to cover up her embarrassment.

"Well that's good," Chuck stated. "We're not strangers."

The girl laughed. "Really? I don't even know your name," she replied.

That threw Chuck for a loop. Girls _everywhere_ knew his name. He was _Chuck Bass_ for God's sake!

"I'm Chuck Bass," he pronounced boldly. The girl's face still showed some sign of recognition but she opened her mouth to speak.

"I'm Caitlin… Caitlin Shaw," she said quietly.

"So…" Chuck smiled. "Caitlin Shaw. What are you doing walking the streets carrying all that stuff?" he teased.

"I had to pick up all the school stuff for my brother and I. It's gorgeous out so I figured I'd walk." The girl smiled, the first true smile Chuck had seen out of her. "Not such a hot idea on the way back," she laughed humbly.

She gave the driver the directions to her family's penthouse and Chuck raised his eyebrows. "My offer to be your tour guide is still valid," he murmured.

Caitlin glared at him, exasperated again. "No," she asserted. "No, not ever! Look… If that's all you want, then I better leave-"

Chuck hastily interrupted her. "No, don't do that. How about this?" The girl raised her eyebrows. "I'll show you around the city or at least keep you in the loop for a while. I won't push anything," he promised without thinking.

Caitlin looked at him skeptically. "This is my stop," she told the driver. She gathered her things and stepped out of the limo. "Fine," she agreed to Chuck. "Partly because you saved me today with the lift and partly because, honestly, I really _don't_ know my way around here." She walked toward the doorkeeper and turned around.

"One question though," Caitlin asked from her front steps. "If you know you're not going to get in my pants, why do you insist on showing me around?"

Chuck didn't answer her. He had been wondering the same thing himself.


	3. Chapter 3: A Challenge

**Unattainable**

**Gossip Girl**

**Chapter Three: A Challenge**

**Agent in Lilac**

**--**

**I do not own Gossip Girl or any of its characters!**

**--**

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"Oh Chuck, you naughty boy! What am I going to do with you?"

"Maybe I need to teach you a lesson"

It was three o'clock in front of school, and two high-pitched giggles filled the air. Chuck Bass looked smugly at the two girls in front of him. Both were obnoxiously batting their eyelashes and twirling their fake-blond hair, trying to look sexy and seductive for the young Bass.

The taller girl glared at the shorter one, "Or _I_ can teach him a lesson Tiffany," she snapped.

The short one, Tiffany, narrowed her eyes and retorted, "_I _offered first Britt!"

The girls stared at each other angrily for a moment until Chuck interrupted. "Ladies, ladies," he purred. "I promise you, there's enough Chuck Bass to go around for everyone."

The two blonds glanced at each other and smirked; the taller one stepped closer to Chuck, until she was pressed against his side. "I have an idea. How about all three of us get together tonight and we can all have a little fun," she whispered in his ear.

The shorter girl apparently had the same idea and closed in on Chuck's other side. He smirked and was about to nod…

Until he caught sight of another blonde walking down the steps of the school. Caitlin traveled effortlessly down the stairs, looking confident and gorgeous. She glanced over and caught Chuck's eye, then, noticing the two skanks next to him, raised her eyebrows, unsurprised, and looked away.

Caitlin didn't mean anything by it, but Chuck still felt a little upset that she seemed to _expect_ him to act like a player.

He continued to watch her, forgetting about the two girls next to him. She reached the bottom of the stairs and started to head toward the street, when a familiar walking figure bumped into her. Chuck glowered when he recognized James. He was using one of his signature moves: James bumped into a girl, acted sorry and cordial, and got the girl to go home with him.

Unfortunately for James, Caitlin was not so easy of a target. Chuck watched as the two chatted affably for a minute until James casually started the moves. Caitlin's pose changed into her familiar huff of indignation and anger and she turned away from James, marching across the commons and into a waiting cab.

Chuck grinned as James's face twisted into an alien expression of rejection. The girls beside him looked put out as Chuck's attention was focused elsewhere and moved a couple feet away, whispering questions as to why Chuck Bass wasn't responding to their tempting offer.

Wiping any sign of Caitlin's refusal off his face, James turned around and spotted Chuck standing by the fence. He smiled and loped over to him.

"Hey man, what's happening?" asked James playfully.

"I just watched you get rejected," Chuck responded satisfactorily. He was glad that he wasn't the only one to be rejected by the blonde.

James's face became confused again. "Yeah, I don't get it," he admitted. "Those moves have never failed me before." He thought for a second and winked, "Hey, but at least you landed her, right man!"

James's assumption sobered up Chuck's lighthearted mood. He replied back quietly and coldly, "No, she turned me down too."

James looked stunned, then thrilled. "So pretty much a smokin' hot new girl comes and gives us both our first rejections ever… Do you know what that means?" Chuck shrugged, and James gave a predatory Cheshire grin, "A challenge," he answered.

That turned the conversation off for Chuck. For any other girl, he would have agreed to a bet or thought of the chase as a hunt, but for some reason, it bugged him to think of her as his prey. Most of all, it bugged him that _James_ thought of it that way.

Chuck huffed and decided to get his mind of the topic and grabbed both of the fake-blonde skanks and headed toward his limo. The girls got in eagerly, excited to have his attention again.

For some reason, James's last statement stuck with both of the young bachelors. Chuck was frustrated and tried to put it out of his mind by focusing on the two girls in his limo. Meanwhile, unfortunately for Chuck, James was planning. After all, Caitlin was a challenge. And there was nothing James loved more than a challenge.


	4. Chapter 4: Reflections

Gossip Girl

Chapter Four

"Mindset"

Agent in Lilac

I do not own Gossip Girl or any of the characters

Chuck Bass and Nate Archibald sat casually together, eating lunch in a corner of the school's courtyard. They hung out at the same table every day. It was perfect, because they had privacy but could still see everyone else in the quad.

"I just didn't say anything and let him finish his speech. It's not like he hasn't told me where he wants me to go to college a million times before," Nate continued talking about his father's college pressure as Chuck zoned out, instead scanning all the ladies in the area.

Tiffany, one of the blonde tramps he took home yesterday, caught his eye and waved, but Chuck didn't acknowledge her. She anxiously pulled out a compact mirror to check her makeup, confused as to why she couldn't hold the young Bass's attention after their night together. Chuck continued his skim and huffed; none of these girls were interesting.

"But at least it's over, right?" finished Nate. He looked expectantly at his friend and, noting his frustrated expression, scrunched his eyebrows. "Hey, is everything okay man?" he asked.

Chuck shrugged his shoulders and thought for a moment. "I'm confused," he stated seriously.

"About what?" questioned Nate.

Chuck glanced around once more to make sure nobody was in hearing range. He looked at Nate intently and lowered his voice. "Look around you," he whispered.

Nate skimmed over the gorgeous, privileged teenagers in the courtyard but didn't notice anything extremely different. He tilted his head to show that he didn't know what Chuck was inferring to.

"The ladies," explained Chuck. "None of them seem… appealing to me."

Nate raised his eyebrows, surprised. Chuck said lots of crazy things, but this seemed to top them all. In all their years as best friends, Nate had never heard Chuck uninterested in women. Even the shallow, desperate girls would have perked up Chuck's ears a little bit. Nate didn't know what had changed.

"Did something happen?" he asked.

Chuck deliberated on this question, unsure whether he wanted to admit the happenings of Saturday night. Chuck always got whatever girls he wanted; he had never faced this little thing called rejection before, and he wasn't quite sure how to handle it.

"So you remember that party Saturday night that I went to?" Chuck asked. Nate nodded, unsure as to what Chuck was getting to. He dropped his voice even lower, "Well, there was this girl there, and she was my target for the night… and I didn't land her."

Nate looked at his best friend's bewildered face and offered his best solution to console him. "Well, maybe you were having an off night? It happens to everyone, even Chuck Bass."

Chuck huffed in irritation, "That's not it!" he growled. "I gave her all my best moves and executed them perfectly."

"Does she have a boyfriend? That could be it?" Nate suggested.

"No she definitely does not," Chuck answered assertively. "She just rejected me, and-"

Chuck stopped talking as he saw a familiar blonde figure loping towards their table.

"What's happening guys?" James asked as he sat down between Chuck and Nate.

With that, Nate scrunched his eyebrows. He did not like James one bit and did not understand why Chuck remained friends with him. He thought James was shady and not someone to be trusted. Nonetheless, Chuck kept him around, and Nate just avoided seeing him as much as possible.

"Just checking out the hot new freshmen this year," Chuck answered back cockily. He could discuss the new girl with Nate, but his friendship with James was much more competitive, and he couldn't let him see that this girl got to him.

"Aw why are you even bothering?" James laughed arrogantly. "You know that girl Caitlin puts all of them to shame. And we've got a challenge to think about too."

Nate noticed Chuck tense up slightly and guessed that this must be the girl who Chuck was talking about earlier.

"Oh, her? I haven't given her much thought… I know as soon as I come her way, she'll come crawling all over me," Chuck responded lazily. Little did James know that Chuck was wondering how he could possibly win this challenge, because Caitlin, for some reason, seemed dead set against hooking up with him.

"Ah we'll see, we'll see," James smiled. He loved the idea of this girl rejected the two of them; getting girls had gotten too easy, and he loved the chase of getting this unattainable one.

The lunch bell rang then, and all the students in the courtyard rose up and slowly headed back in to class. James headed toward math, while Chuck and Nate turned the other way towards history.

"Don't let that guy get to you," Nate said. "You can win this, you're Chuck Bass, and it's not like she can hold out forever." He didn't really support what the challenge entailed, but he hated seeing his best friend so confused and wanted to help him get back to his confident self. Nate walked into his history class, and Chuck strolled down the hall toward the school's exit, lost in his thoughts.

"Skipping Bass?" Chuck turned around as he heard a familiar voice that had been haunting him the past couple days. He instantly changed his face from brooding to his familiar expression of arrogance and boredom and instantly felt like himself again.

"Yes Shaw. I have places to go, people to see," Chuck drawled back.

Caitlin's eyebrows rose as she fell into step next to Chuck. Chuck couldn't help but notice that she looked great in her school uniform, though he would never mention that to her face.

"Yeah but don't you also have classes to go to?" Caitlin asked back with raised eyebrows. "Or does Chuck Bass have more important things on his agenda?"

Chuck rolled his eyes at the blonde. "Yes, always. It's something you need to know about me," he drolled. "There are lots of things you can get to know about me, if you want," he suggested.

Caitlin shot Chuck one of her glares. "All I need to know is my way around the city. Hopefully I've made this clear already… or I could find someone else. There are some really nice people here, I mean –"

"Don't get your panties in a twist Shaw," Chuck replied smoothly. "I promised to show you around, and nobody else around here really knows the city like I do."

Caitlin shook her head with a smile, "Okay, fine. Are you free tomorrow, because I really need to start getting this place down."

Chuck nodded, "I'm a busy guy, but I think tomorrow works."

"Okay perfect," she replied. "After school is best for me, so I'll see you tomorrow. I've got to head to class."

And with that Caitlin turned around and sauntered down the hall towards the classrooms. Chuck noticed that almost every boy turned around to check out the new girl, though Caitlin herself didn't seem to notice or care.

She was a girl guys were clearly interested in, which made Chuck think. Maybe James was right in his thinking – Caitlin was a challenge, so hooking up with her would be especially satisfying. He was already seeing her the next day, so he was one step ahead of James already. Winning this bet would both end all of his unsettling feelings of rejection and allow him to finally beat James once and for all. He just had to be more subtle about it. Chuck realized his normal tactics wouldn't work on this new girl – it would take all the best moves to land her, but he knew he was the man for the job.


End file.
